Kailua vacation rentals

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Select from 184 houses, 66 apartments, and other vacation rentals to find the perfect place for your stay in Kailua. Vacation rentals provide the best amenities for your family, friends, or furry companion, like air conditioning and WiFi. You'll be sure to find a rental that has what everyone needs, including options that are accessible or non-smoking.

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The laid-back Kama’aina lifestyle in Kailua

Called Kailua Town by residents, Kailua is a buzzing beach community where a laid-back lifestyle is the rule. If turquoise water and white sand on Oahu’s windward coast aren’t enough for you, jump into trendy boutiques, stop off at popular eateries, and hang out with the kama’aina (locals) at the Thursday evening farmers’ market. Distinctive ingredients put a twist on the island cuisine here, and unique boutiques offer treasures to commemorate your stay in any one of the Kailua vacation rentals.

An Aloha adventure in Kailua

Water is the watchword here, and Lanikai Beach or Kalama Beach Park, the Kawai Nui Marsh wetlands, or Maunawili Falls may just float your boat. From stunning sunrises to spectacular sunsets, the 1-mile Lanikai Pillbox hike offers a sweeping panoramic view of land and sea from concrete bunkers, built between WWI and WWII as part of Oahu’s coastal defense system. And, within a stone’s throw of the shore, Moku Nui, Moku Iki, and Flat Island are a meditative mantra to while away the hours on the silky soft sand of Kailua Beach. Experience all the warmth and hospitality of the Aloha spirit at family-friendly Kailua vacation rentals.

Land and sea is all you need in Kailua

Surf, kitesurf, windsurf, or kayak are the best ways to explore this area. Kailua Beach is a reef-protected bay where beauty and safety reign supreme, so swimming and snorkeling are stress-free. Head out for a hike or a round of golf in this lush, green paradise. Take a picnic blanket, and enjoy local favorites as you listen to live music at the Kailua Farmers’ Market. If you’re a fan of the slower island pace, Kailua has the small-town vibe that delivers an authentic Hawaiian experience. Kailua vacation rentals offer the calm you crave and the family fun you want.

A tropical paradise in Kailua

With an annual average temperature of 71°F, inching up to 80 or so in summer, any season is a good time to visit Kailua. Lush and tropical, passing showers in winter months won’t dissuade you from hanging loose under the sun, and coastal trade winds will temper any high humidity in summer. Keep in mind that high season in Hawaii runs from mid-December through March or mid-April, since snowbirds from colder climes like to wing their way to paradise at that time, though Kailua is still somewhat of an Oahu hideaway.

Kailua—a natural beauty

Located on the leeward side of the Nu’uanu Pali peak, crescent-shaped Kailua Bay is sheltered from the hustle and bustle of Honolulu. Crystal blue water and silky white sand invite visitors to come and stay awhile. Meaning heavenly sea in Hawaiian, Lanikai Beach is another mile-long stretch that is a favorite of many locals. Once the center of life for early Kailuans, the Kawai Nui Marsh is a protected wetland, providing a habitat to many wildlife species, and a peaceful trail. Hike in Maunawili Falls are the most accessible in Oahu and cascade 15 to 30 feet into a cool mountain pool.

Transportation to and around Kailua

The nearest airport is in Daniel K. Inouye Intl. Airport (HNL), located 12.6 mi (20.2 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Kapolei, HI (JRF-Kalaeloa), which is 22.2 mi (35.7 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Kailua?

Based on our research, houses are the most desirable vacation rental type in Kailua. But naturally, everyone's idea of an epic stay isn't going to be the same. Vrbo has vacation rentals of all shapes and sizes, so you're sure to discover your perfect match.

How much does it cost to rent a vacation rental in Kailua?

Different things affect what you'll pay for your vacation rental in Kailua, such as the season, length of stay and type of property. But, all of our vacation homes have something in common — incredible value. Just add your travel dates to find your perfect match.

How much does it cost to rent a beach house in Kailua?

When you travel and the size and style of the property will influence how much you'll pay for your beachside escape. Enter your Kailua travel dates to see all your options on Vrbo. Did someone just say "hot tub"? Use the filters to pick the features and amenities you want in your beach house.

What are popular rental amenities in Kailua?

Some of the most popular rental amenities people search for in Kailua are a sauna, a barbecue grill and ski-in/ski-out facilities. Whether you're vacationing with family, pals or even pets, Vrbo vacation properties feature the best amenities for fun and relaxation with the people that matter most.

What are the top attractions for families in Kailua?

There are lots of amazing things to do and see with the family in Kailua, such as:

  • Kailua Beach
  • Lanikai Beach
  • Waimanalo Beach

Can I find two-bedroom vacation rentals in Kailua?

Kailua has 28 two-bedroom vacation rentals to choose from. Discover a vacation home with all the comfort and privacy you're looking for at a price that's hard to resist on Vrbo.

Are there vacation rentals with WiFi in Kailua?

Kailua has 91 vacation rentals with WiFi, so you can stay connected while traveling. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with the family to catching up on social media, these Vrbo homes make it a cinch to go online.

How old do you have to be to rent a vacation rental in Kailua?

The minimum age requirements can vary across properties on Vrbo, so look at the rules of the vacation rental in Kailua you want to book. But in general, it's 16, 18 or 21.

How long can I rent a vacation rental in Kailua for?

The amount of time you can stay in a Kailua vacation home for depends on the property. Simply put in your travel dates to find available options offering longer term stays. They include the things you need to make your extended getaway more enjoyable like kitchens and yards. Some Vrbo vacation homes may also offer weekly or monthly discounts, so you can stay even longer for less.

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